Looking back on my career, I realize that I drove my various bosses crazy from time to time. Always without meaning to. In fact, it’s pretty easy to do.
So, if you have a particularly annoying boss and nothing to lose by seeing if you can drive them crazy, then here are some ways to do it without even having to try hard.
On the other hand, if you’re conscientious about your career and would NEVER want to upset your boss, then keep these in mind as things to stay away from.
And of course, remember that every boss is different, so the things that annoy one person may be less offensive to another.
Use these at your peril or your pleasure!
1. Needing lots of “couch time”
You could be one of those needy people who are so insecure that you’re regularly in the boss’ office for reassurance and pats on the head. I had a team member like that. He was constantly in my office for his dose of “I’m okay, you’re okay”.
I tended to be the opposite – someone who rarely went to the boss for reassurance even though I totally needed it. In fact, I needed it on steroids! But it’s not good to be as stoic and “not in your boss’ office” as I was. But that’s another story.
2. Doing the “disappearing act”
You could be hard to find. One of those Dilbert cartoon characters that excels at hiding from the boss and anyone else for that matter.
I had someone on my team who no one could ever find. And yes, it drove me nuts. Was the guy out interviewing? Was he going to quit and make me look bad? No one knew where he was – not his assistant, not his team members, and probably not even his wife! And that’s definitely another story.
3. Not getting to the point
This one was one of my “guilty as charged” problems. I would tell the whole story from beginning to end, with the conclusion coming only after 3-5 torturous minutes.
Just like holding your breath, listening for 3 minutes straight can be life-threatening and torturous, especially for type A bosses who are trying to be “nice”.
This also works in email format. Just draft a super long email, single-spaced, with the conclusion all the way at the bottom of the email.
This one – being long-winded – is especially effective because no one can accuse you of deliberately driving the poor boss crazy!
4. Not knowing your numbers
This one I did by accident, but it definitely got my boss upset. He’d ask for something that surely I’d know cold. But I didn’t and he was embarrassed in front of the client.
This one is tricky because it really can backfire and reflect badly on you too. But in the right situations, this can make your boss look like they have not trained up their team adequately.
5. Taking on their role
I accidentally upset my boss by inviting the entire department to my house for a summer outing. I thought I was being generous and welcoming, but I hadn’t gotten him in on the deal, so it was really me inviting the group he should have hosted. And once I had done that, he couldn’t very well complain because it would look petty.
This is just the kind of thing that will truly upset your boss without his or her being able to say a word, unless they want to risk looking like an insecure, petty tyrant.
6. Making your boss mop up after you
I had a coworker who was a big producer but had terrible interpersonal skills. As a result, he would leave a big group of upset people in his wake. His boss constantly had to smooth over the ruffled feathers of other departments.
For a while, it was worth it because the guy brought in so much business. But after a few dry years, it was a different story. So this one has risks too. But enjoy it while you produce!
7. Expecting your boss to solve every problem
This one is especially effective if you have a super nice boss. She or he will spend lots of time listening to your problems and brainstorming with you. They will want to be helpful. And it’s only over time that they will realize how much of their time you are wasting.
By the way, I was that boss when I first started. That’s how I know!
This won’t work on more experienced bosses because they’ll already know to make you come to them with proposed solutions and options. But use this on those unsuspecting nice people in their first management role.
8. Having really bad hygiene
This is one of those insufferable situations where your boss will find it almost impossible to say anything. But it will be driving him or her crazy. Especially if they have an acute sense of smell. Which I do! There’s nothing worse than having someone brief you with terrible body odor or bad breath. (As an aside, while it’s not a hygiene problem, the same goes true for wearing too much cologne or perfume, so you can be hygienic and still drive your boss crazy.)
And if you also cause a problem with others, then you’ll be causing your boss even more of a headache because then she’ll be forced to come and say something. I know because I’ve had to have those conversations. Do you know how embarrassing it is to tell someone they need to shower more? Or wear more supportive undergarments?
9. Not dressing the part
I caused my boss headaches when I just didn’t have the right attire, which made me harder to promote. The poor guy had to go in front of the promotion committee and get shot down while making a case for me, partly because I hadn’t bothered to invest in a proper wardrobe.
While I wasn’t in on the discussion, I’m guessing that it contributed to people questioning whether I really was Managing Director material. Obviously, much more goes into it. But I was putting up obstacles that didn’t need to be there by still buying the same clothes and shoes as I would in my early days.
So if you’re indifferent about promotion, this can make life difficult for your boss by making it harder for them to push for your advancement.
10. Pretending you understand when you don’t
During a busy period, I was seconded to a team covering KKR, the top-flight private equity firm. The team was under time pressure to produce an analysis of covenants on some bonds, which involved looking through about 10 sets of legal documents and summarizing the key terms.
I was asked to do this in the 3 hours before heading off to the client meeting. “No problem,” I said, even though I had never read a bond covenant before.
When I got back to my desk with the pile of documents, it became clear that I didn’t know how to read through the legalese. Instead of asking for help, I muddled along and ended up completing a fraction of the analysis.
At the meeting, it turned out to be a major point of interest for KKR and therefore a big embarrassment for the team leader. I still feel terrible about it, but I’m afraid it was even worse for my boss. I never was asked to “help” that team again.
Those are just 10 of the great ways to drive you boss crazy if you really want to. Or 10 things to avoid if you’re trying to make a good impression.
What other ways have you found to drive your boss crazy? And what drives you crazy when you’re the boss?
Leave a comment and let me know. And have some fun with this one!